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Pete Holmes on Crashing and Finding God in Filthy Jokes

“Please don’t be uncomfortable,” beseeched the comedian Pete Holmes moments after sharing the story of that time his life imploded when the wife he’d married at 22—“not that uncommon in my Christian College, evangelical church world”—cheated on him, and left him for her lover.

Holmes, now 37, has a high tolerance for trying to make people comfortable in uncomfortable moments. You may know him from his podcast, You Made It Weird With Pete Holmes, on which he draws guests into very, very long conversations, and grills them on squirm-inducingly personal subjects (two questions he recently asked Andy Samberg: a) when did you lose your virginity, and b) did you wear a condom?)

We were on the topic of Holmes’s real failed marriage because a fictionalized version of that scenario is now the premise of his new Judd Apatow–produced HBO show, Crashing. “I had, like ten years to ruminate on it,” he said, “and to get enough of a zoomed-out perspective to start thinking about how I could make it funny, and how I could write my wife as a sympathetic character.”

Time, as they say, heals all wounds, and also, as they don’t really say, makes them hilarious. Crashing is about an unemployed aspiring comedian named Pete, a six-feet-five classic Apatowian man-child, who hasn’t quite figured out how to square his devoutly conservative Christian values with the secular profanity of the stand-up world. In the meantime, he’s living off the generosity of his elementary school teacher wife Jess (Lauren Lapkus), who grows more resentful with every two-drink-minimum, open mic night her husband pays to tell jokes at.

“You’ve been doing this for so long. Shouldn’t your act be better by now?” she wails just after Pete comes home early one day, and catches her in bed with a new age-y art teacher named Leif (George Basil), with whom Jess intends to move to Tampa. In short order, Pete’s settled, safe, suburban existence is upended, and he finds himself homeless, penniless, and thrown headfirst, sink or swim, into the punishing New York City comedy scene.

There’s a lot of sinking, and only a few hints that Pete may one day prove buoyant. The show’s title is a double entendre: Crashing is what he does pretty much every time he’s on stage. (Sample joke: “What do you think the employee discount is at the dollar store? Do you think it’s just, take it?”) But each episode also sees him meeting another new comedian, and asking to crash on his or her couch. Hence the show’s incredible roster of guest stars: Artie Lange, Pete’s first savior; T.J. Miller, and Sarah Silverman, to name a few.

The comedy world according to Pete Holmes can be brutal, sure (case in point, the MC who cruelly convinces him to pull a Tig Notaro and process his emotions on stage mere hours after finding Jess with Leif), but it can also be silly and familial and as cozy as Sesame Street. Seen through Pete’s rosy, possibly deluded perspective, it’s a tiny community of familiar faces, people whose jokes may be dirty, whose dispositions may be surly, but who are ultimately willing to come to one another’s rescue. In other words, it’s the kind of place where everyone—not just stand-up super fans—might want to spend some time.

“All comedians are trying to do is having their thoughts, their feelings, their ideas, be validated," Holmes attested. "They wanted to be authentic and honest, and be appreciated for it.”

“Comedians,” he added, “can be effective empty vessels for what you’re going through in your life. The benefit is they can be funny about it.”

When the real Pete Holmes’s life fell apart, was there a real Artie Lange who took you in?

Yeah, real Pete Holmes had like five or six real Artie Langes. There are elements of comedy that can be competitive and back stab-y, but one of the underreported sides is that we love each other and help each other, kind of like a messed up extended family. I’ve helped people in the way Artie helped me on the show, and I’ve been helped by people, some of whom are on the show. Like TJ Miller. He was shooting a movie right after my wife left me, and I went and lived with him at a hotel in Pittsburgh for a week, just because he didn’t want me to be alone.

There are a lot of club owners and older comedians who haze or exploit Pete, and justify it by saying that it will make his comedy better. Do you buy into that, or is there a better way?

It’s kind of the Lorne Michaels approach, being the withholding dad makes the performer rise to the occasion. I think it’s both. I think comedians are exploited because we are so eager, and we will perform for free, and we will hand out fliers. But the truth is, the suffering we all go through, that’s one of the reasons comedians are a family. We love talking about how we had to bark [handing out fliers for stage time]. Sarah Silverman actually barked on the same corner I barked on, which is the same corner we shot on in the show, which is very surreal.

Is it harder to write bad jokes that are still sort of funny than it is to write good jokes that are actually funny?

I’m super happy to say that it’s not that hard to write bad stand-up. I guess the trick is to write bad stand-up that sounds like you’re trying to be good. They say in acting when you’re crying, the real trick is to act like you don’t want to cry. You can’t act like you’re trying to cry because people who cry are trying not to cry. Pete has to bomb, but he has to look like he’s trying to kill.

Fortunately I have notebooks and notebooks and notebooks of old jokes that will sound very much like I’m trying to do well and that, I promise you, will not work.

I can’t think of a lot of shows that are for a mainstream audience made by someone from a Christian background who is grappling with his faith. What were you hoping people would take from that?

I think it’s interesting that a lot of times television networks will veer in the complete opposite direction from anything faith-based, especially Christianity. But I was excited at the opportunity to broach that subject. It’s such a huge part of why I think the show works. Pete’s wife leaves him, and the next scene is not him getting drunk, or trying to meet girls at a bar, or having some anonymous sex. He’s a guy who never ever expected this to happen to him, and he doesn’t have the tools to cope with it, and a lot of that has to do with how he sees the world, how he understands religion and god. For me, and I don’t think it will ever be super overt, the show is about breaking up with his wife, breaking up with his parents, and breaking up with his traditional understanding of god. Those are three very interesting breakups. Two out of three would be okay, but I’m glad that HBO and Judd are bold enough to let us play in that third space, because that’s the most interesting one to me.

It felt like you phrased that very carefully. What’s your relationship to Christianity now?

I did phrase that carefully. I’m a Christian, Buddhist, Hindu, Jewish guy. I’m a spiritual whore. I’ll take psychedelic mushrooms if I think that’s going to get me in the room with the big guy. Or I’ll do yoga or meditate or chant. I’ll go to a Catholic mass. I’ll surf. I’ll ski. I’m just so fascinated with the mystery of existence.

And there’s really no way, including atheism, that I’ve encountered that isn’t deeply fascinating to me. That’s where I’m at now. I like to say I’m Christ-leaning, meaning that’s the story I enjoy. I learned that story first. There’s a certain familiarity I have with Jesus and the Gospels and the Bible that I enjoy reclaiming in a new, not dogmatic, not literal, beautiful, metaphorical, mysterious way that Pete in the show would find downright heretical and incorrect. But I’m far happier and more free and open and honest than I’ve ever been in my life, and that probably has a lot to do with my openness to finding god almost anywhere, including in a filthy dick joke.

There’s some really smart casting here. Like, for example, Gina Gershon as an Artie Lange groupie who Pete accidentally goes home with, and deeply offends when he’s unwilling to sleep with her.

Honestly, every time there’s a brilliant stroke of casting, whether Artie Lange, or Gina, or Lauren Lapkus, that was all Judd. Gina didn’t even audition. Judd was just like: It should be Gina Gershon.

She was so great. We used all these things we riffed. She had this thing where she goes: You’re making me feel bad! We’d been improvising for like, four hours at that point. She was running on empty. She was just saying exactly what she was thinking. You made me feel bad! That was so much funnier than the perfect, well-written joke. It’s just this woman having a real meltdown. Pete’s a people pleaser. His worst nightmare is someone being like: You’re hurting my feelings.

So what did you learn about making TV from Judd Apatow?

Honestly, he’s so clear about it. He learned from Garry Shandling that the whole point is to make sure it’s honest. And then you worry about making it funny. So we would try and write scenes and situations that had a core of truth. It didn’t necessarily need to be what happened to me. But you made sure it felt grounded, and then we could improvise, make jokes, try and make each other laugh.

You do three versions of the scene while shooting. You shoot the one that’s scripted. You do the one that’s looser but more serious. And then you’d do one that’s looser and you make every single joke you could possibly think of. I was surprised that often, Judd would favor a scene more straight than the version that was more like an episode of 30 Rock, with a joke every second.

Is Crashing really just a way to lower expectations, so that people who come see your real stand-up will be pleasantly surprised?

That is something I hadn’t considered until just now. That’s the best comedy set up you can have. You never want people expecting you to be amazing. It’s always good for people to come and say, “Oh, I hope it’s okay,” and then you exceed their expectations. That’s the comedian’s dream.